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Catalytic enantioselective protonation of enol trifluoroacetates by means of hydrogenocarbonates and cinchona alkaloids.

The Journal of organic chemistry (2011-06-18)
Aurélie Claraz, Jérôme Leroy, Sylvain Oudeyer, Vincent Levacher
RESUMEN

Herein is disclosed an efficient catalytic enantioselective protonation of enol acetates by means of a readily implementable transition-metal-free chemical process. By making use of simple hygrogenocarbonates as the proton source and hydroquinine anthraquinone-1,4-diyl diether as the chiral proton shuttle, a series of cyclic enol trifluoroacetates are protonated under mild conditions to yield the corresponding ketones in up to 93% ee.

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Sigma-Aldrich
Hydroquinine, 98%
Sigma-Aldrich
Hydroquinidine hydrochloride, 98%